EP2730565A4 - Tumor targeted drug combretastatin a4 derivative - Google Patents

Tumor targeted drug combretastatin a4 derivative

Info

Publication number
EP2730565A4
EP2730565A4 EP12807451.5A EP12807451A EP2730565A4 EP 2730565 A4 EP2730565 A4 EP 2730565A4 EP 12807451 A EP12807451 A EP 12807451A EP 2730565 A4 EP2730565 A4 EP 2730565A4
Authority
EP
European Patent Office
Prior art keywords
derivative
targeted drug
tumor targeted
combretastatin
drug combretastatin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP12807451.5A
Other languages
German (de)
French (fr)
Other versions
EP2730565A1 (en
EP2730565B1 (en
Inventor
Yong Wang
Cang Zhang
Xiaorong Liu
Yan Zhang
Yunyun Wang
Wenping Zhang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nanjing Sanhome Pharmaceutical Co Ltd
Original Assignee
Nanjing Sanhome Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nanjing Sanhome Pharmaceutical Co Ltd filed Critical Nanjing Sanhome Pharmaceutical Co Ltd
Publication of EP2730565A1 publication Critical patent/EP2730565A1/en
Publication of EP2730565A4 publication Critical patent/EP2730565A4/en
Application granted granted Critical
Publication of EP2730565B1 publication Critical patent/EP2730565B1/en
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
EP12807451.5A 2011-07-05 2012-07-04 Tumor targeted drug combretastatin a4 derivative Not-in-force EP2730565B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201110186688 2011-07-05
CN201110422678.5A CN102863388B (en) 2011-07-05 2011-12-16 Tumor targeted drug Combretastatin A4 derivatives
PCT/CN2012/000921 WO2013004075A1 (en) 2011-07-05 2012-07-04 Tumor targeted drug combretastatin a4 derivative

Publications (3)

Publication Number Publication Date
EP2730565A1 EP2730565A1 (en) 2014-05-14
EP2730565A4 true EP2730565A4 (en) 2015-04-29
EP2730565B1 EP2730565B1 (en) 2017-04-26

Family

ID=47436477

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12807451.5A Not-in-force EP2730565B1 (en) 2011-07-05 2012-07-04 Tumor targeted drug combretastatin a4 derivative

Country Status (10)

Country Link
US (1) US9139574B2 (en)
EP (1) EP2730565B1 (en)
JP (1) JP5875679B2 (en)
KR (1) KR101579093B1 (en)
CN (1) CN102863388B (en)
AU (1) AU2012278750B2 (en)
BR (1) BR112013033452A2 (en)
CA (1) CA2839942C (en)
MX (1) MX344663B (en)
WO (1) WO2013004075A1 (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103889964B (en) * 2011-07-05 2016-03-02 南京圣和药业股份有限公司 Tumor-targeting drug Combretastatin A4 derivative
CN104418821A (en) * 2013-08-22 2015-03-18 四川大学华西医院 2,4-substituted 5-(3,4,5-trimethoxyphenyl) thiazole derivative and preparation method and application thereof
CN104771371B (en) * 2014-01-14 2021-02-19 南京圣和药业股份有限公司 4- (3, 5-dimethoxyphenyl) -5- (3-hydroxy-4-methoxyphenyl) imidazole preparation
CN104771396B (en) * 2014-01-14 2019-04-26 南京圣和药业股份有限公司 The application of 4- (3,5- dimethoxy phenyl) -5- (3- hydroxyl -4- methoxyphenyl) imidazoles
CN105017321A (en) * 2014-04-18 2015-11-04 南京圣和药业股份有限公司 Crystal forms of diphenyl imidazole anticancer drug and preparation method thereof
CN105017325A (en) * 2014-04-18 2015-11-04 南京圣和药业股份有限公司 Crystal form D of diphenyl imidazole anticancer drug and preparation method thereof
CN105017324A (en) * 2014-04-18 2015-11-04 南京圣和药业股份有限公司 Crystal form N of diphenyl imidazole anticancer drug and preparation method thereof
CN105017322B (en) * 2014-04-18 2018-09-28 南京圣和药业股份有限公司 The preparation method of diphenyl-imidazole kind anti-cancer drugs object
CN105017323A (en) * 2014-04-18 2015-11-04 南京圣和药业股份有限公司 Crystal form A of diphenyl imidazole anticancer drug and preparation method thereof
GB201706806D0 (en) 2017-04-28 2017-06-14 Sentinel Oncology Ltd Pharmaceutical compounds
CN109453123B (en) * 2018-11-19 2021-05-11 中国药科大学 Combretastatin derivative freeze-dried powder injection and preparation method thereof
CN111116571B (en) * 2019-12-27 2022-07-12 吉首大学 Compound containing oxazole and triazole diheterocycle and preparation and application methods thereof
WO2022236253A1 (en) * 2021-05-03 2022-11-10 Nuvation Bio Inc. Heterocyclic compounds as kinase inhibitors

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002050007A2 (en) * 2000-12-21 2002-06-27 Cancer Research Technology Limited Substituted stilbenes, their reactions and anticancer activity
WO2005007635A2 (en) * 2003-07-18 2005-01-27 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Combretastatin derivatives with cytotoxic action
WO2010132498A1 (en) * 2009-05-11 2010-11-18 Oxigene, Inc. Vascular disrupting agents for treatment of polypoidal choroidal vasculopathy

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4996237A (en) 1987-01-06 1991-02-26 Arizona Board Of Regents Combretastatin A-4
US5561122A (en) 1994-12-22 1996-10-01 Arizona Board Of Regents Acting On Behalf Of Arizona State University Combretastatin A-4 prodrug
TW334418B (en) 1995-03-07 1998-06-21 Ajinomoto Kk Stilbene derivatives and pharmaceutical compositions
US6201001B1 (en) * 1999-08-02 2001-03-13 Abbott Laboratories Imidazole antiproliferative agents
CN101130539B (en) * 2007-09-26 2012-05-30 浙江大学 Indole-substituteing imidazoline-2-ketones derivant, preparing method and uses of the same
CN101230079A (en) 2008-01-29 2008-07-30 中国海洋大学 1,2-glycoside transderivative of oxazole compounds and preparation method thereof
CN101230074A (en) 2008-01-29 2008-07-30 中国海洋大学 Phosphate derivative of oxazole compounds and preparation method thereof
CN101602730B (en) * 2008-06-12 2013-06-19 北大方正集团有限公司 Substituted imidazole derivative
CN102190625B (en) 2010-03-18 2013-08-28 南京圣和药业有限公司 Stilbene tumor targeted medicine Combretastatin A4 analogs
JP5636091B2 (en) * 2010-05-05 2014-12-03 ウニベルジテート バイロイト Combretastatin analogs for use in cancer therapy

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002050007A2 (en) * 2000-12-21 2002-06-27 Cancer Research Technology Limited Substituted stilbenes, their reactions and anticancer activity
WO2005007635A2 (en) * 2003-07-18 2005-01-27 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Combretastatin derivatives with cytotoxic action
WO2010132498A1 (en) * 2009-05-11 2010-11-18 Oxigene, Inc. Vascular disrupting agents for treatment of polypoidal choroidal vasculopathy

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LE WANG ET AL: "Potent, orally, active heterocycle-based combretastatin A-4 analogues : synthesis, structure-activity relationship, pharmacokinetics, and in vivo antitumor activity evaluation", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 45, 1 January 2002 (2002-01-01), pages 1697 - 1711, XP002304485, ISSN: 0022-2623, DOI: 10.1021/JM010523X *
See also references of WO2013004075A1 *

Also Published As

Publication number Publication date
MX344663B (en) 2017-01-04
US20140128384A1 (en) 2014-05-08
CN102863388B (en) 2015-04-29
CN102863388A (en) 2013-01-09
AU2012278750A1 (en) 2014-01-30
BR112013033452A2 (en) 2017-10-31
KR20140044878A (en) 2014-04-15
KR101579093B1 (en) 2015-12-21
EP2730565A1 (en) 2014-05-14
CA2839942A1 (en) 2013-01-10
CA2839942C (en) 2016-10-11
US9139574B2 (en) 2015-09-22
MX2013015120A (en) 2014-10-17
JP2014523885A (en) 2014-09-18
WO2013004075A1 (en) 2013-01-10
AU2012278750B2 (en) 2015-03-05
JP5875679B2 (en) 2016-03-02
EP2730565B1 (en) 2017-04-26

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